Electrophile-induced rearrangement of 1,2,4-trioxanes. Formation of 1-benzofuran and 2H-1-benzopyrans

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Abstract
3,3,6,10b-Tetramethyl-4a, 10b-dihydronaphtho[2,1-e][1,2,4]trioxane and its 3,3-spirocyclic cyclopentane analogue on treatment with an excess of trimethylsilyl trifuloromethanesulphonate for 10 min at 24 °C rearrange to give 2-(2-oxopropyl)-3-methyl-1-benzofuran in high yield; in similar fashion the 3-methyl, n-butyl, and phenyl derivatives of 3,10b-epidioxy-2,3,4a,10b-tetrahydro-6-methyl-1H-naphtho[2,1-b]pyran give the 3-oxobutyl,3-oxoheptyl, and 3-phenyl-3-oxopropyl derivatives of 2-formyl-3-methyl(2H)-1-benzopyran.

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